Hydroxy-ethylamino salts of 3-acetylamino-4-hydroxy-benzene-arsonic acid



Patented May 24, 1932 UNITED STATES PATENT OFFICE KARL STREITW'OLF, OF FRANKFORT-ON-THE-MAIN, ALFRED FEHRLE, OF BAD-SODEN- ON-THE-TAUNUS, AND WALTER HERRMANN AND PAUL FBITZSCHE, 0F FRANK- FORT-ON-THE-MAIN, GERMANY, ASSIGNORS TO WINTHROP CHEMICAL COMPANY, INC., 01 NEW YORK, N. Y., A CORPORATION OF NEW YORK HYDROXY-ETHYLAMINO SALTS OF 3-ACETYLAMINO-4-HYDROXY-IBENZENE-ARSONIG ACID No Drawing. Application filled January 4, 1930, Serial No. 418,648, and in Germany June 14, 1929.

The present invention relates to hydroxyethylamino salts of 3-acetylamino-4r-hydroxy-benzene-arsonic acid.

We have found that the 3-acetylamino-lhydroxy-benzene-arsonic acid used to a great extent in the therapy of syphilis forms with hydroxy-ethylamine well crystallizing salts which are readily soluble in water. Our new salts have, in contradistinction to the hitherto known salts of this acid, the advantage that the human body has a better tolerance to them, that they have an enhanced solubility and a greater stability in solution. They are, therefore, well suited for use in medicine, especially for the treatment of children. The salts formed need not first be isolated, but the solutions obtained by combining the components in an aqueous median may be used directly. In order to increase the stability of the solutions it is advisable to add small quantities of sodium sulfite t0 the solutions.

The following example serves to illustrate the invention, but it is not intended to limit it thereto.

droxyethylamlno arsonic acid of the following probable formula NH.O0.0H|

crystallizes out. It is filtered by suction, washed with alcohol and ether and dried in a vacuum. The product forms a white crystallized power which is soluble in 1.5 to 2 ONH:.CH2.0H2OH O=As V ONHLOHLCHZOH is obtained.

We claim:

1. As new products hydroxy-ethylamino salts of 3-acetylamino-4-l1ydroxy-benzenearsonic acid being well crystallized compounds, rather readily soluble in water, diflicultly soluble in acetone, ether and benzene.

2. As a new product, the salt of the following probable formula:

NHO0.0H:

formed by the action of one molecule of hy droxy-ethylamine upon one molecule of 3- acetylamino-4-hydroxy-benzene-arsonic acid,

being a white crystallized powder which is soluble in 1.5 to 2 parts of water of 35 C. 1'.

and diificultly soluble in acetone, ether and benzene.

3. As a new product, the salt of the following probable formula:

NH.OO OH:

formed by the action of two molecules of hydr-oxy-ethylamine upon one molecule of 3- acetylaminoA-hydroxybenzene arsonic acid,

being a white crystallized powder, well soluble in water and difiicultly soluble in acetone, ether and benzene.

In testimony whereof, we afiix our signatures.

KARL STREITWOLF. ALFRED FEHRLE, WALTER HERRMANN PAUL FRITZSCHE. 

